Watch Sailing & Boating Adventures Around the World
Explore sailing, boating, and water sports through our curated video archive. From epic sea voyages to serene diving escapes, discover unforgettable adventures from top YouTube creators. Start your journey. Dream big. Sail far.
⛵ In this episode we leave paradise behind and sail back to civilisation to reprovision for our next adventure.
We stock up the boat, have fun with exotic fruit, and come face to face with giant monster fish. Join us for a mix of real cruising life, culinary chaos and wild encounters 😅
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We’re a family sailing full-time, exploring the Caribbean and Central America aboard our sailing catamaran Big Lost. New episodes every Tuesday at 10:30 AM ET.
In this episode aboard Sailing Big Lost, we finally trade the noseeums of Snug Harbor for sunshine, clear water, and one of the most iconic...
We’re a family sailing full-time, exploring the Caribbean and Central America aboard our sailing catamaran Big Lost. New episodes every Tuesday at 10:30 AM ET.
We’ve had rain off and on since arriving in Panama, and as we begin exploring the San Blas—now learning their true name, the Guna Yala Isla...
We’re a family sailing full-time, exploring the Caribbean and Central America aboard our sailing catamaran Big Lost. New episodes every Tuesday at 10:30 AM ET.
We’re a family sailing full-time, exploring the Caribbean and Central America aboard our sailing catamaran Big Lost. New episodes every Tue...
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Join Sailing Liberty as they tackle crucial boat preparations and exciting upgrades for their upcoming adventure to the Florida Keys and beyond! See them renew essential ship documents, em...
We’re a family sailing full-time, exploring the Caribbean and Central America aboard our sailing catamaran Big Lost. New episodes every Tuesday at 10:30 AM ET.
In this episode of Sailing Big Lost, we head inland for a change of scenery—trading the Caribbean coast for the lush mountains of Minca, Co...
We set sail from Grenada to Bonaire on our Vision 444 catamaran for the final leg of our passage west. The trip begins as smooth downwind sailing—perfect conditions, fresh mahi on the grill, dolphins dancing at the bow, and plenty of laughs with our buddy boat.
But of course, no sail is complete wi...
After a month of boat work and marina life in Grenada, it’s finally time to say goodbye to friends and set sail west toward Bonaire! This passage is extra special because it’s our first downwind sail on our Vision 444 catamaran, and we’re eager to see how she performs.
With the weather on our side, ...
After some much-needed time on the hard at Clarke’s Court Marina in Grenada, SV Big Lost is finally splashed back into the water! 🚤🌊
We tackled a few essential boat projects, including servicing our Gori Prop with the help of our good friend and fellow Vision owner, Michael. With the work complete,...
We set sail from the British Virgin Islands, taking on one of the most challenging points of sail: east into the trades. As we make our way to Sint Maarten, we reflect on the many passages that have brought us to this point—and why it always seems like we’re heading against the grain.
With our sigh...
After picking up long-awaited spare parts in the US Virgin Islands, we leave Honeymoon Bay behind and set sail for the British Virgin Islands—our next stop on the journey south to Grenada for hurricane season.
Our first destination: Norman Island, where we blow off some steam at the infamous floati...
Our girl sailing crew dive for conch and experience the raw, real side of off-grid life in the Bahamas. Living on a sailboat isn’t always glamorous—but it's always an adventure! The girls get covered in conch 💩 and take an off grid shower.
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After our 7-day passage to the USVI, we find ourselves in island time — waiting on delayed packages before we can continue our journey south to Saint Martin for hurricane season. While we wait, it’s a week of boat projects and island adventures!
We spend time troubleshooting a radar that won’t acti...
After 7 days and 2 hours at sea, we finally made landfall in Saint Thomas!
This was our longest passage yet — and our first without extra hands on deck — so we’re incredibly proud to have safely navigated 1,051 nautical miles as a family. Along the way, we battled rough seas and squalls, replaced a ...
After months of chaos—selling a boat, buying a new one, and surviving endless shipyard setbacks—we’re finally on the move. But we’re late. Hurricane season officially began on June 1st, and we’re already behind schedule.
Rather than take the traditional Thorny Path through the Caribbean, we’ve chos...
After weeks of stress and setbacks at Harbour Towne Marina, the moment we've been waiting for is finally here—we're pulling the dock lines and setting sail for the very first time aboard our brand new 2023 Vision 444 catamaran!
Our destination: Xquisite Marina in Freeport, where the rest ...
This week hit hard. After being told the marina would cover the damage they caused during our haul out—damaging our sail drive and prop—we got a call no boat owner wants: the general manager overruled the previous decision. Now, we're left with the full bill. Another crushing blow in what’s fel...
After months of dreaming, planning, and searching… we finally bought a boat! 🥳 This episode is packed with all the wild and wonderful moments that led up to closing on our new Vision 444 catamaran — our floating home for the next chapter of our sailing adventures.
We kicked things off with a thrill...
From the snowy mountains of Idaho to the turquoise waters of the Caribbean, Conor’s life has always been about chasing adventure. Dirt bikes, skiing, waterskiing, hunting, and sailing — his childhood was packed with energy, freedom, and a growing love for the outdoors.
In this video, Conor shares h...
Every journey has a beginning—and an evolution. In this episode, we take a trip down memory lane to share how we got here, from dreaming of life on the water to making it a reality. We say goodbye to Big Lost, our first catamaran, as we close escrow and hand her over to her new owners.
But don’t wo...
✨Selling our boat comes with its challenges! In this video, we’re sharing the results of the buyer’s survey, the necessary repairs, and the negotiations we had to make. From unexpected fixes to finalizing the deal, this is a behind-the-scenes look at what it takes to sell a boat.⛵️
⚓ Want to learn ...
In this episode, we set sail from Nassau, cruising through the beautiful Berry Islands on our way to Freeport for a critical moment-the boat survey and sea trial! Along the way, we hook a few fish 🐟, soak in the stunning blue water, and enjoy the sailing life.
Once we arrive at Xquisite Marina in F...
Big changes are on the horizon 🌅 for the crew of Sailing Big Lost! In this episode, we reveal some exciting news about our future while exploring the stunning Exumas Sand Flats 🏖️, witnessing an epic SpaceX launch 🚀, and bracing for an incoming storm 🌊. Life on the water is always unpredictable, and...
Join us on sailing adventure as we explore the stunning U.S. Virgin Islands (USVI) aboard our aluminum sailboat and sail to the British Virgin Islands (BVI) . In this episode, we were hoisting the sails in whichever direction where the wind takes us even if it means backwards or double the mileage. ...
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Technical or functional cookies are essential for the basic functionality of the website. They are necessary for general web administration, session identification, website security, and presenting optimized content based on your devices. They also improve the general usability of the website, enabling features such as logging in to your account, adding products to your shopping cart, and checking out securely. These cookies are crucial for the website to function properly and cannot be switched off in our systems. They are typically set in response to actions made by you, such as setting privacy preferences, logging in, or filling in forms. While you can configure your browser to block or alert you about these cookies, please note that some parts of the site may not work properly if you do so. It’s important to mention that these cookies do not store any personally identifiable information directly related to your identity. We may place these cookies without your explicit consent as they are strictly necessary for providing our service.
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The technical storage or access is necessary for the legitimate purpose of storing preferences that are not requested by the subscriber or user.
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